What Bill Simmons Taught Me About Blogging, Podcasting, And Modern Journalism

Matt K. Lewis Senior Contributor
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There’s a lot of handwringing in journalism these days about how hard things are in the business. And rightly so. Things have changed. Just as creative destruction and globalization upended a lot of American jobs, technological changes have changed journalism. There are winners and losers. You can either clutch your pearls and lament this, or you take advantage of the new system. After all, the old rules had gatekeepers that kept people like me out (it also kept some people out who really deserved to be kept out; these things are always a double-edged swords).

One of the other people who would have been kept out was a Boston kid named Bill Simmons. Were it not for the internet, he’d probably still be bartending and regaling townies and college buddies with stories about the Pats or his encyclopedic knowledge of pop culture. Instead, he’s a (soon-to-be-unemployed) multi-media juggernaut.

Here’s what I like about Bill Simmons: He writes columns, he hosts a podcast, he talked ESPN into launching a sports-meets-pop-culture vanity project for him called Grantland, he helped conceive ESPN’s terrific “30 for 30” documentary series. In short, he tackles a lot of interesting projects — and he hustles.

He’s entrepreneurial — or, actually, the better word for the way he approached his job at ESPN is “intrapreneur.”

He also has a posse. Simmons is pals with a pretty interesting cadre, ranging from Jimmy Kimmel to Adam Carolla to Tony Kornheiser. (I’ve already written about what I learned about writing from Kornheiser, but like Simmons, Carolla has an entrepreneurial spirit, likes to hustle, and has shown an ability to diversify his work product.)

After losing his job as a morning radio host, Carolla decided to be his own boss. Now, he hosts several regular podcasts (his main show, one with Dr. Drew that is reminiscent of the old “Love Line” show, a home repair show called “Ace On the House,” an automotive podcast  called “Car Cast,” and — for premium listeners — a long-form interview podcast on leadership and career/life advice, called “Take a Knee“). Carolla has written several books, and also sells his own beverage product called “Mangria,” hosts a Spike “docu-reality” show called “Catch a Contractor,” makes movies like “The Hammer,” “Road Hard,” and most recently directed the terrific new documentary, “Winning: The Racing Life of Paul Newman.”

Celebrities like Howard Stern and Glenn Beck probably remain bigger names than either Simmons and Carolla, but while their transition to alternative media (in Stern’s case, from terrestrial radio; from Beck’s case, from a popular Fox News show) might have resulted in more money and freedom, it also made them less relevant to a mainstream audience. Because Simmons and Carolla more or less came up in a new or alternative media environment — boosted by the support of their loyal fans — they have even less to lose by abandoning a large media institution.

If you haven’t guessed, part of the reason I’m a fan of these shows is that I’m not just listening for content, I’m also observing their process. Simmons works in the sports journalism world and Carolla is more a comedian, but that doesn’t mean there aren’t things to learn. (Let me highly recommend a recent podcast where Bill Simmons talks about “his journey to joining ESPN.com.”) How have I tried to replicate some of the lessons of Simmons and Carolla? Whether it’s launching a podcast, spending ridiculous amounts of time on Twitter, writing a book, co-hosting Bloggingheads, or diversifying by writing for various outlets, I’ve tried to embrace some of this same “free agent nation” ethos in politics that they perfected in sports and entertainment (albeit, at a lower level; Bill Simmons has like 3.7 million Twitter followers, after all).

This is perhaps the trend of the future. More and more, we can expect to see journalists who have cultivated some degree of a personal “brand” (I realize there is no way to talk about someone’s brand and not sound douchey) not only choose to remain unattached to bigger outlets, but in some cases, actually leave them. We saw this happen when Nate Silver left the New York Times (!) for ESPN. And — even before Ezra Klein split the Washington Post for Vox — my friend and colleague Ben Domenech was insisting that Ezra Klein should quit the Post, for exactly these same reasons. “When you look at how people are following news these days,”Domenech said on my podcast, much of the stuff “is fed through the lens of Twitter and Facebook, and who you follow and who you like on those platforms, and not going to the front page of sites anymore.”

I’ve been blessed; rather than having to go out on my own, I’ve become a bit of an intrapreneur. I have a terrific regular gig here, but also get to experiment with a bunch of side projects. It’s really the best of both worlds.

Earning this degree of freedom didn’t happen over night, and — of course — it is still somewhat fraught with danger. Bill Simmons serves as a warning to anyone who believes that his status entitles him to commit acts of insubordination. I think it was gutsy to call out the NFL commissioner, but it was stupid to essentially dare ESPN to say anything about it. With great freedom, comes great responsibility.On the other hand, I have a feeling this kid’s gonna be okay. And, ironically, what happened to him at ESPN is yet another argument for diversifying and seizing control of your own brand.

Matt K. Lewis